Trifluoroacetic acid → N-[2-(3-Aminopropyl)-6-chloro-5-quinolinyl]-cyclohexaneacetamide

HRID 2217817Notes

Reaction equation

HRID 2217817 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([NH:30][C:31](=[O:39])[CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)[CH:13]=[CH:12]2>ClCCl>[NH3:15].[NH2:22][CH2:21][CH2:20][CH2:19][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([Cl:8])[C:10]=2[NH:30][C:31](=[O:39])[CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[N:15]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86609738[3-[6-Chloro-5-[(cyclohexylacetyl)amino]-2-quinolinyl]propyl]-carbamic acid 1,1-dimethylethyl ester

Product 2

HCID 222AmmoniaYield 10%HCID 11268393N-[2-(3-Aminopropyl)-6-chloro-5-quinolinyl]-cyclohexaneacetamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of [3-[6-chloro-5-[(cyclohexylacetyl)amino]-2-quinolinyl]propyl]carbamic acid, 1,1-dimethylethyl ester (Example 23(a)) (0.9 g) in dichloromethane (15 mL). After stirring for 2 hours the solvent was removed under reduced pressure and the resulting residue was purified (Varian Chem elute cartridge with dichloromethane as eluant). Further purification (Varian SCX cartridge using methanol (100 mL) and then 10% ammonia in methanol (100 mL) as eluant) afforded the title compound (300 mg).

Workup

  1. customwas removed under reduced pressure
  2. customthe resulting residue was purified
  3. wash(Varian Chem elute cartridge with dichloromethane as eluant)
  4. customFurther purification (Varian SCX cartridge

Sources & evidence

ORD record
ord-ac9483e6d4b14ee9bdd0b76bea38204e
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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